3-Hydroxypyridine → Tert-butyl 2-(pyridin-3-yl)oxypropionate

HRID 566447ノート

反応式

HRID 566447 の反応式
[H-].[Na+].[OH:3][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1.Br[CH:11]([CH3:19])[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].C(=O)(O)[O-].[Na+]>CN(C=O)C>[N:6]1[CH:7]=[CH:8][CH:9]=[C:4]([O:3][CH:11]([CH3:19])[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:5]=1

参加物

6

反応物 4

HCID 79713-HydroxypyridineHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 545327tert-Butyl 2-bromopropanoate

生成物 1

HCID 22668079Tert-butyl 2-(pyridin-3-yl)oxypropionate収率 62%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒3 回

実験手順

To a suspension of 1.20 g of sodium hydride (60% oil dispersion; 30.0 mmol) in 10 mL of dry DMF at room temperature were added dropwise 2.85 g of 3-hydroxypyridine (30 mmol) in 10 mL of dry DMF, maintaining the temperature below 40° C., and the mixture was stirred at room temperature for 90 min. Under ice-cooling, 6.28 g of tert-butyl 2-bromopropionate (30 mmol) in 10 mL of dry DMF were slowly added dropwise, maintaining the inner temperature within 5 to 10° C., and then the mixture was warmed to room temperature with stirring for 4 hours. After neutralizing with saturated sodium bicarbonate aq., the mixture was extracted with ethyl acetate. The organic layer was washed with water and then saturated brine, dried and evaporated. The residue was purified by column chromatography on silica gel (eluent: n-hexane:ethyl acetate=2:1) to give 4.15 g of tert-butyl 2-(pyridin-3-yl)oxypropionate (Yield: 62%) as a brown oil.

後処理

  1. temperaturemaintaining the temperature below 40° C.
  2. temperatureUnder ice-cooling
  3. temperaturemaintaining the inner temperature within 5 to 10° C.
  4. temperaturethe mixture was warmed to room temperature
  5. stirringwith stirring for 4 hours
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe organic layer was washed with water
  8. dry with materialsaturated brine, dried
  9. customevaporated
  10. customThe residue was purified by column chromatography on silica gel (eluent: n-hexane:ethyl acetate=2:1)

出典と根拠

ORDレコード
ord-1580d532c97a4e91abeaa3e915abd642
出典データセット
uspto-grants-2001_01
特許番号
US06174905B1

反応ノート

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